Digital transformation strategies that work – stories from 13 DX leaders

On the topic of digital transformation, it’s never too long before a shocking statistic rears its head: 70% of digital transformations (DX) projects ultimately fail.

With worldwide spend on DX expected to reach $3.9 trillion in 2027, according to the International Data Corporation, organisations are actively pursuing their transformation agendas despite the significant levels of failure identified by McKinsey’s research. The big question is how can they beat the odds?

Digital Transformation Conference London

At the Digital Transformation Conference in London hosted by Roar, it wasn’t long before that 70% statistic was mentioned. As the speakers took the stage, each with different business challenges, they shared the strategies they use to ensure digital transformation success in their organisations.

Themes of growth-oriented strategies, customer-centric transformations, the critical role of visionary leadership, the need for agile methodologies, and the crucial role of storytelling in facilitating change were prevalent across the discussions.

Let’s take a look at the key insights and themes from these 13 digital transformation leaders’ personal experiences.

#1 Mastercard’s digital transformation growth focus

Tom Harris, SVP Digital Business Transformation, Mastercard, shared how the company is navigating its digital transformation by focusing on a growth-centric strategy, underpinned by data-driven decision-making and AI. Harris explains, "We don't call it digital transformation, we call it our growth operating system because primarily everything we do in the company is about growth."

Under this system, Tom Harris’s leadership extends to a structured approach to designing, developing, and delivering products that aim to sustain and amplify the company's growth objectives.

Data-driven decision-making

Data plays a pivotal role in Mastercard's operations with over 100 billion transactions processed annually. This wealth of data was initially focused externally to assist customers, but a shift occurred about a decade ago when they began to leverage this data internally. "The only way to make sense of that is to use data and data-driven insights to kind of guide our prioritisation efforts, guide our conversations, guide our strategy in a really thoughtful way," Tom asserts.

Cultural and leadership challenges

The integration of data into decision-making also brought cultural challenges. Tom discussed how data challenges the traditional storytelling approach of leadership based on anecdotes rather than hard facts. "Data is not plural of anecdote, which is what I find myself telling our leaders all the time," he points out.

Role of AI and technology

Looking forward, Harris highlights the role of AI in enhancing Mastercard's capabilities. AI is seen not just as a tool but as a strategic asset that could predict future trends and help make more informed decisions. "The real promise of AI is that the data we have at the moment tells me where I’ve been and tells me where I am, but AI has the potential to tell me where I'm going," he explains. There is significant interest in using AI to project future scenarios, helping prioritise resource allocation more effectively.

#2 Drive towards digital-first customer experience at Maersk

James Brindley-Raynes, Head of Digital Customer Journey at Maersk, reflected on the importance of having a clear and compelling product vision and strategy: one that not only guides the team internally but also aligns with broader organisational goals.

The global shipping company’s digital transformation has two clear objectives. They want to attract a new audience, especially targeting the untapped SME market, aiming to make interactions more streamlined and accessible through digital platforms.

Maersk also wants to revamp existing customer journeys. This involves transitioning from a heavily person-dependent set up to self-serve, digital-first experiences from initial registration to complex transactions like booking and payment, resembling functionalities seen in e-commerce platforms.

The importance of agile and fast iteration

Agile methodologies are central to Maersk’s approach, allowing for iterative development. Brindley-Raynes says that engaging with customers directly to gather feedback and continuously iterating based on this input is crucial for refining digital strategies and ensuring they meet the actual needs of the users. "You want to fail fast or learn quickly. You’ve got your hypothesis, you build, you test it, get your feedback from your customer," he says. This methodology helps in quickly identifying what works and what needs adjustment, minimising risks and enhancing product relevance.

#3 Quick wins in digital transformation at the UK Post Office

The UK Post Office's slide at the Digital Transformation Conference in London titled "Retail technology transformation landscape on a page"

The UK Post Office is undergoing a significant digital transformation

Zdravko Mladenov, the UK Post Office’s former Group Chief Digital and Information Officer, shared insights from his experience leading a significant digital transformation. The focus is on modernising the Post Office infrastructure, enhancing digital services, and integrating innovative solutions such as mobile devices for postmasters.

Technological overhaul and customer service enhancement

Mladenov discussed the dual focus of updating the technological infrastructure to support a wide array of services, including banking, financial products, and government services, and enhancing the accessibility and efficiency of services provided in remote locations. "We need to think not just about the products and services, we need to think about connectivity, resilience of the technology," he says.

Quick wins and long-term goals

Customer-centricity was a key factor in the Post Office digital transformation, with the aim to enhance service delivery through digital platforms, particularly to improve accessibility for remote areas.

The introduction of new technologies aimed to streamline operations and improve customer interactions, demonstrating the critical impact of strategic vision and quick wins in achieving successful transformation outcomes. "Quick wins matter a lot more than perhaps you might instinctively think," Mladenov says.

Key role of leadership in digital transformation

Regardless of quick wins, Mladenov emphasised the importance of leadership in steering the transformation efforts, particularly the need to align the extensive technological changes with the broader business goals.

The importance of vision and leadership

The transformation journey at the Post Office was not without its challenges, particularly in aligning extensive technological changes with the broader business goals. Zdravko Mladenov highlighted the critical role of visionary leadership in managing these comprehensive transformations. "It is very important to maintain that vision. Keep iterating it for your team," he advises.

#4 Did somebody say digital transformation?

Just Eat's slide at the Digital Transformation Conference in London titled "Takeaways; pun intended"

Just Eat's digital transformation has delivered some impressive takeaways using storytelling techniques

Carlos Galán from Just Eat discussed the integration of FinOps within the organisation to enhance operational efficiency across 300 engineering teams. With 900 million orders processed last year, the need for reliability and cost-effective operations is paramount.

The focus was on using storytelling as a powerful tool to communicate and engage teams in optimising cloud spend and operations. "Using narratives to frame our financial strategies has significantly increased engagement and compliance," he says.

Enhancing operational efficiency through digital transformation

Galán also discussed the challenges of managing large-scale data and the strategies to mitigate information overload, which he refers to as avoiding the "Tony Stark Syndrome."

"We're trying to move away from a centralised model to be able to drive efforts at scale," he notes, emphasising the shift towards more scalable and efficient operational models.

By embedding viral elements and utilising social media strategies in corporate communications, Carlos Galán shared how Just Eat has successfully made FinOps a key part of the engineering culture.

This approach has not only improved cost efficiency but also significantly increased the engagement of teams with FinOps initiatives. The results included a substantial decrease in cost per 1000 orders by 21%, demonstrating the tangible benefits of the storytelling approach.

#5 Nationwide improvements from digital transformation

Robin King, Head of Enterprise Architecture at Nationwide, detailed the company’s journey towards a more simplified, agile, and data-driven operation, focusing on cloud capabilities as a backbone for technological modernisation.


King highlighted the dual challenge of managing legacy systems and embracing innovative solutions that disrupt traditional financial services; "Modernisation is about disrupting financial services, providing new propositions, new journeys," he says.


Need for clear communication

Robin King covered the strategic role of enterprise architecture in aligning technology initiatives with business objectives, emphasising the importance of clear, simplified communication strategies that resonate across all levels of the organisation. "We need to make our strategies understandable not just to technologists but to the entire leadership," he says.


By adopting a data-centric approach, Nationwide aims to refine its technology roadmaps and better forecast and manage demands, particularly in cloud services. King also discussed the regulatory and skills challenges associated with cloud adoption and how Nationwide is addressing these through strategic planning and stakeholder engagement.


#6 Primark’s shift to digital agility

Tom Rooney's slide at the Digital Transformation Conference in London titled "Reprting of progress to goals drives the right conversations"

Tom Rooney, Primark, says tracking performance weekly in accessible performance dashboards helps to keep the digital transformation strategy on track

Tom Rooney, Head of Digital Product, Primark, discussed how the retailer is undergoing a digital transformation that isn't just about technological upgrades, but a fundamental shift in corporate culture and operational strategies.

Primark's 18-month journey from bricks-and-mortar retail to a full e-commerce solution and robust digital engagement is driven by a change in how teams are structured and projects are approached. Tom Rooney elaborates: "We've transitioned from a traditional project management approach to a more dynamic, product management-oriented approach." This shift is crucial for nurturing a culture that embraces continual change and innovation.

Building a robust digital infrastructure

At the heart of Primark’s transformation is the construction of a sophisticated digital infrastructure which supports a composable commerce architecture. This infrastructure enhances Primark’s operational efficiency and customer service. Rooney says, "Digital transformation is as much about cultural change as it is about technological change."

Strategic partnerships and collaboration

Rooney emphasised the importance of viewing colleagues not as mere stakeholders but as partners in the digital journey, fostering a collaborative environment that's essential for the success of digital initiatives. "We're all heading in the same direction, aiming to achieve a unified goal," Rooney notes, highlighting the alignment of digital objectives with broader business goals.

#7 Funding Circle’s digital-first strategy

Valeria Kontor's slide at the Digital Transformation Conference in London titled "Staying ahead of the curve"

Valerie Kontor, Funding Circle, shares achievements from the SME lending company's digital transformation

Valerie Kontor, Product Manager, Funding Circle, shared insights on how digital technologies are revolutionising the financial services industry, particularly in the SME lending space.

Revolutionising SME lending

Valerie highlighted how Funding Circle has transformed the lending process for SMEs through digital innovation. "Transitioning to a digital-first approach has revolutionised our SME lending processes," Valerie notes, emphasising the significant reduction in loan approval times and simplification of the application process.

Leveraging advanced technologies

The integration of machine learning and data analytics has been pivotal in enhancing loan assessment accuracy and customer service. Kontor explains: "Leveraging technology, we're transforming not just processes but also enhancing experiences and outcomes."

Challenges and market impact

Despite substantial growth, expanding market awareness remains a challenge. Valerie Kontor discussed strategies for future growth, focusing on continuous innovation and adaptation to meet evolving market demands and technological changes.

#8 Building blocks of digital transformation at Kingfisher plc

Chris Blatchford, CTO at Kingfisher plc, explained how technology is being utilised to drive innovation in the customer experience and efficiency within the company which includes household names such as B&Q.


Customer-centric technology solutions

The Kingfisher plc focus is on customer-centric solutions where technology directly addresses customer needs, enhancing satisfaction and loyalty. "Our goal is to develop solutions that exceed our customer's expectations," Blatchford says, adding that data analytics is key to understanding customer behaviours and preferences, which informs product development and marketing strategies. "Innovation is not just a buzzword; it’s a necessity in today’s technology landscape,” he adds.

Agile methodologies underpin transformation

Underpinning the digital transformation is the strategic use of agile methodologies to quickly respond to market demands and enhance operational flexibility. "Agile methodologies empower our teams to adapt quickly to changes in the market."


Blatchford also emphasised the importance of cross-functional collaboration in fostering innovation and ensuring that technological advancements align with Kingfisher’s broader business goals, including sustainability efforts.


Commitment to sustainability

Touching on how sustainability is integrated into Kingfisher plc’s technology strategies, he described initiatives designed to reduce the company’s carbon footprint through smarter use of technology and resources, aligning with broader environmental goals.

#9 Every little story helps digital transformation at Tesco

Christopher Harvey's slide titled "Campaign approach to change marketing"

Christopher Harvey, Tesco, uses a campaign approach to change marketing to improve impact and outcomes

Christopher Harvey, Head of Change, Tesco, shared a unique strategy for implementing change management, taking inspiration from digital marketing techniques. Treating change initiatives like well-crafted marketing campaigns can lead to higher success rates by effectively informing, engaging, and motivating all stakeholders involved.

"Change management should be like a marketing campaign," he says, stressing the importance of building understanding through digital channels and engaging employees effectively to foster acceptance and participation in change initiatives.


Visual appeal in communications

Highlighting the power of visually appealing content, Harvey pointed out that well-designed materials significantly increase engagement and participation in change initiatives. "If you build it they will come, but make sure it's visually appealing," he says, underscoring the necessity of crafting attractive, compelling content that grabs attention and maintains interest throughout the change process.


Personal connection and humour

In Harvey’s experience, the use of stories in particular can enhance receptivity to new ideas and practices. By humanising the process, he makes the case that change management can become more relatable and less daunting for everyone involved.


# 10 Citizens Advice embraces AI to enhance service delivery

A seated audience watching a presentation displayed on screens in front of them

Alex Butler, Executive Director Digital, Citizens Advice, shared insights into the organisation's strategic approach to digital transformation with an emphasis on AI integration to streamline operations and improve service delivery. "AI offers tremendous potential for enhancing how we deliver advice and interact with those who need us most," Butler says.

For example, Citizens Advice developed an AI tool through ChatGPT to assist advisers in providing timely and accurate advice when they're in meetings with clients. Previously advisers searched for answers on the website which Butler says had grown into a behemoth over time and wasn’t necessarily able to provide quick answers. AI is proving to be a better solution.


Ethical considerations in AI deployment

However, the deployment of AI within Citizens Advice comes with a strong emphasis on ethical considerations. "It’s crucial to approach AI integration with a clear understanding of the ethical implications," Butler notes, underscoring the need for careful consideration of data privacy and security.


Future outlook on technology integration

Looking ahead, Alex Butler outlines future initiatives to further integrate technology for good in the organisation. The goal is to make services more personalised, better supporting individuals in need. "Our journey towards digital transformation is about making our services more accessible and efficient," she says.


#11 Fusion of digital and business strategy

Sanjay Patel's slide titled "Difference between business and digital strategy"

Sanjay Patel connects digital initiatives directly to the drivers of shareholder value highlighting the difference between business strategy and digital strategy

Sanjay Patel, former Group Chief Information Officer, Tate & Lyle, emphasised the critical alignment of digital strategy with overall business planning, advocating for digital transformation to be viewed as an integral part of business strategy. "Digital strategy is business strategy written for the world of digital," he says, highlighting the necessity for digital initiatives to be deeply integrated into the business framework.

Collective ownership of digital efforts

Stressing the importance of collective ownership of digital strategies, Patel says the entire executive team should embrace digital initiatives rather than isolating them within the IT department. "Ownership of the digital agenda should be a collective effort by the leadership team, not just the CIO or CTO," he explains.


Adapting to organisational readiness

Discussing the importance of aligning the pace of digital transformation with an organisation's readiness, he advocates for a measured approach: "The pace and success of digital transformation depend significantly on organisational readiness and cultural alignment," he says.


Value-driven digital transformation

To gain traction, Sanjay Patel connects digital initiatives directly to the drivers of shareholder value, ensuring that each step of digital transformation contributes positively to the company's goals. "Always link digital initiatives to tangible business outcomes to ensure they deliver real value," he advises. Digital strategies need to have a clear impact on business performance.


#12 Needs-focused digital transformation

Like many of the other leaders, Lisa Topliss, Director of Digital Workplace, Ricoh, emphasised the importance of aligning digital transformation with organisational and customer needs, ensuring that all efforts enhance user and customer experiences. "Digital transformation should focus on creating value for customers," rather than focusing solely on technological advancements.


Challenges of implementation

Topliss shared her experiences with digital initiatives that did not meet expectations, underscoring the lessons learned from these challenges. "Learning from failed digital initiatives is just as important as celebrating successes," she says, advocating for an open and learning-focused approach to tackling digital changes.


Incremental and value-driven change

At Ricoh, taking an incremental approach to transformation and integrating feedback effectively was a proven strategy to manage risk: "Always aim for incremental improvements rather than sweeping changes to mitigate risks," Topliss suggests. This methodical approach to digital updates allows for adjustment and optimisation based on ongoing evaluation.


Engagement and effective communication

Stressing the necessity of clear communication and active stakeholder engagement, Lisa Topliss says: "Effective communication is key to successful digital transformation” and the smooth integration of new digital tools and practices.


#13 Adaptive access and identity management

Adam Preis, Director of Product and Solution Marketing, Ping Identity, highlighted the growing significance of adaptive access and identity management as key differentiators in enhancing customer experiences and securing user interactions across platforms. "Privacy is not just compliance; it's a competitive advantage in enhancing customer trust and personalisation," he notes.

Challenges of traditional access methods

Highlighting the limitations of traditional access methods, which often involve rigid and inflexible systems, he said, this approach can hinder user experience and impede organisational agility. Preis discussed moving towards dynamic authorisation to allow for more granular and situation-aware access decisions.

Impact on business value

In Ping Identity’s experience, investing in advanced identity management solutions drives significant business value by enhancing customer loyalty, improving security, and ensuring compliance with regulatory requirements. "Investments in identity and access management need to drive not just technical outcomes but real business value," he says.

Recurring themes across digital transformation

It’s interesting to see so much common ground across the 13 senior executives working in digital transformation. Regardless of whether an organisation is B2B, B2C, or public service, we can identify seven recurring themes and challenges.

  • Leadership in digital strategy: The C suite has to own the digital transformation agenda to ensure success. Fostering strong leadership to champion digital initiatives and ensuring alignment with the digital vision across the organisation is key.
  • Customer-centric digital strategies: Customer centricity is a predominant theme. A driving force of change is aligning digital initiatives with customer needs to enhance satisfaction and fuel growth. This involves using data analytics to understand and predict customer behaviours effectively.
  • Adopt data-driven strategies: As part of their digital transformation many businesses are transitioning to data-driven insights, not just to better service customer needs but to guide business direction.
  • Cultural readiness for change: Ultimately, the pace and impact of digital transformation depend on the organisation’s cultural readiness. Comprehensive training and development practices alongside clear and consistent communication are key to success.
  • Utilise storytelling for engagement: There’s a recurring theme of the importance of storytelling to make complex strategies relatable and engaging, effectively communicating the value and vision of digital transformations.
  • Ensure ethical implementation of AI: Deploying and experimenting with AI is emerging as a key element of digital transformation. But this needs to be done through the lens of ethical implications, enhancing service delivery while securing data privacy and customer trust.
  • Embrace organisational agility: Maintaining flexibility to adapt strategies based on feedback and evolving market conditions was a final recurring theme. Organisations are embracing agile, fail fast, learn and iterate approaches to ensure continuous improvement and alignment. For certain legacy companies, this involves embracing, not only a very different skillset, but adjusting to an agile mindset.

While it's no guarantee of success, ensuring the seven areas are included as part of the strategy will certainly help companies on their digital transformation journeys avoid inclusion in the McKinsey 70%.

Karen Hesse

Karen Hesse

Karen Hesse is Founder and CEO of 256, a multi global, award-winning digital strategy agency based in Dublin, Ireland. With over 25 years’ experience helping B2B and B2C brands make informed business and marketing decisions, Karen specialises in using storytelling to grow brand love and guide digital transformation. 
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